US8895779B2 - Processes for producing monoammonium adipate and conversion of monoammonium adipate to adipic acid - Google Patents
Processes for producing monoammonium adipate and conversion of monoammonium adipate to adipic acid Download PDFInfo
- Publication number
- US8895779B2 US8895779B2 US13/086,801 US201113086801A US8895779B2 US 8895779 B2 US8895779 B2 US 8895779B2 US 201113086801 A US201113086801 A US 201113086801A US 8895779 B2 US8895779 B2 US 8895779B2
- Authority
- US
- United States
- Prior art keywords
- bottoms
- maa
- daa
- broth
- solid portion
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related, expires
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/02—Preparation of carboxylic acids or their salts, halides or anhydrides from salts of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
- C07C51/46—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation by azeotropic distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/02—Dicarboxylic acids
- C07C55/14—Adipic acid
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
TABLE 1 | |||
Run # | 1 | ||
Name of Acid | Adipic | ||
Wt Acid Charged (g) | 14.62 | ||
Moles Acid Charged | 0.1 | ||
Wt 28% NH3 Solution Charged (g) | 12.14 | ||
Moles NH3 Charged | 0.2 | ||
Wt Water Charged (g) | 800.75 | ||
Wt Distillate (g) | 350.46 | ||
Wt Residue (g) | 466.65 | ||
% Mass Accountability | 98.8 | ||
Wt % NH3 in distillate (titration) | 0.15 | ||
Moles NH3 in distillate | 0.031 | ||
% Total NH3 removed in Distillate | 15.5 | ||
% First NH3 removed in Distillate | 31 | ||
DiNH4/MonoNH4 | 69/31 | ||
Final Pot Temp (° C.) | 100 | ||
Micromoles of NH3/g distillate | 89 | ||
Initial Wt % ammonium salt | 2.2 | ||
pKa1 | 4.43 | ||
pKa2 | 5.41 | ||
pKa3 | NA | ||
Claims (24)
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13/086,801 US8895779B2 (en) | 2010-04-30 | 2011-04-14 | Processes for producing monoammonium adipate and conversion of monoammonium adipate to adipic acid |
CA2738166A CA2738166C (en) | 2010-04-30 | 2011-04-21 | Processes for producing monoammonium adipate from fermentation broths containing diammonium adipate, monoammonium adipate and/or adipic acid, and conversion of monoammonium adipate to adipic acid |
EP11164486A EP2383250A1 (en) | 2010-04-30 | 2011-05-02 | Processes for producing monoammonium adipate from fermentation broths containing diammonium adipate, monoammonium adipate and/or adipic acid, and conversion of monoammonium adipate to adipic acid |
BRPI1102061-0A BRPI1102061A2 (en) | 2010-04-30 | 2011-05-02 | processes for producing monoammonium adipate from fermentation broths containing diammonium adipate, monoammonium adipate and / or adipic acid, and converting monoammonium adipate to adipic acid |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US32976810P | 2010-04-30 | 2010-04-30 | |
US13/086,801 US8895779B2 (en) | 2010-04-30 | 2011-04-14 | Processes for producing monoammonium adipate and conversion of monoammonium adipate to adipic acid |
Publications (2)
Publication Number | Publication Date |
---|---|
US20110266133A1 US20110266133A1 (en) | 2011-11-03 |
US8895779B2 true US8895779B2 (en) | 2014-11-25 |
Family
ID=44351728
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US13/086,801 Expired - Fee Related US8895779B2 (en) | 2010-04-30 | 2011-04-14 | Processes for producing monoammonium adipate and conversion of monoammonium adipate to adipic acid |
Country Status (8)
Country | Link |
---|---|
US (1) | US8895779B2 (en) |
EP (1) | EP2383250A1 (en) |
JP (1) | JP2013530935A (en) |
KR (1) | KR20130003031A (en) |
CN (1) | CN103153931A (en) |
BR (1) | BRPI1102061A2 (en) |
CA (1) | CA2738166C (en) |
WO (1) | WO2011136941A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20130150551A1 (en) * | 2010-06-16 | 2013-06-13 | Bioamber S.A.S. | Processes for the production of hydrogenated products and derivatives thereof |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012170060A1 (en) * | 2011-06-10 | 2012-12-13 | Bioamber S.A.S. | Processes for producing hexanediol (hdo), hexamethylenediamine (hmd), and derivatives thereof |
CN112439216A (en) * | 2020-12-14 | 2021-03-05 | 河南久圣化工有限公司 | Tertiary evaporation system for recovering dicarboxylic acid from adipic acid waste liquid |
JP7038241B1 (en) | 2021-03-30 | 2022-03-17 | 旭化成株式会社 | Method for producing recombinant microorganism and adipic acid or its derivative |
CN115677476B (en) * | 2022-11-08 | 2023-07-04 | 安徽恒升化工有限公司 | Production process and system of 2-ethylhexanoic acid |
Citations (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1050639A (en) | 1963-09-17 | |||
GB532938A (en) | 1939-06-02 | 1941-02-04 | Rhone Poulenc Sa | Process for the manufacture of adipic nitrile |
US2288687A (en) | 1939-06-07 | 1942-07-07 | Celanese Corp | Manufacture of dinitriles |
GB778253A (en) | 1955-02-02 | 1957-07-03 | Inventa Ag | Process for the manufacture of -e-caprolactam |
US2912363A (en) | 1955-11-28 | 1959-11-10 | Nat Distillers Chem Corp | Fumaric acid fermentation process |
US3063910A (en) | 1960-02-03 | 1962-11-13 | Kyowa Hakko Kogyo Kk | Method of producing l-malic acid by fermentation |
US3433830A (en) | 1964-09-30 | 1969-03-18 | Chevron Res | Aliphatic dicarboxylic acid purification process |
DE1904613A1 (en) | 1968-01-31 | 1969-09-04 | Ici Ltd | Process for the preparation of an aliphatic diamine |
DE1916601A1 (en) | 1969-04-01 | 1970-10-29 | Basf Ag | Process for the production of adipic dinitrile |
US3873425A (en) | 1971-11-19 | 1975-03-25 | Tatsuyoshi Kobayashi | Process for producing itaconic acid |
CA999013A (en) | 1971-06-25 | 1976-10-26 | Du Pont Of Canada Limited | Preparation of hexamethylene diamine |
US4052441A (en) * | 1974-10-10 | 1977-10-04 | Josef Klemens Brunner | Separation of acids and esters in the processing of waste salt solution of cyclohexanone manufacture |
US4082788A (en) * | 1968-10-10 | 1978-04-04 | El Paso Products Company | Esterification and extraction process |
US4105856A (en) * | 1970-09-29 | 1978-08-08 | El Paso Products Company | Recovery process for aqueous waste streams in adipic acid systems |
DE2718363A1 (en) | 1977-04-25 | 1978-10-26 | Roehm Gmbh | Carboxylic acid prepn. from their ammonium salts - by heating in aprotic, dipolar solvent contg. oxygen, to remove ammonia |
DE2729421A1 (en) | 1977-06-29 | 1979-01-11 | Du Pont Deutschland | Polyamide prodn. from adipic acid and hexa:methylene:di:amine - using aq. monomeric nylon salt soln. made using recycle condensate from the autoclave and evapn. stages |
US4238603A (en) | 1977-05-19 | 1980-12-09 | Monsanto Company | Polyamides derived from hexamethylene diamine, terephthalic acid, isophthalic acid and a C5 to C10 aliphatic dibasic acid |
US4254283A (en) | 1979-06-07 | 1981-03-03 | Monsanto Company | Process for preparing adipic acid with recovery of glutaric and succinic acids |
US4271315A (en) * | 1979-11-15 | 1981-06-02 | El Paso Products Company | Treatment of waste stream from adipic acid manufacture |
US4339536A (en) | 1979-06-08 | 1982-07-13 | Nippon Mining Co., Ltd. | Process for the preparation of long-chain dicarboxylic acids by fermentation |
US4400468A (en) | 1981-10-05 | 1983-08-23 | Hydrocarbon Research Inc. | Process for producing adipic acid from biomass |
US4480034A (en) | 1982-06-10 | 1984-10-30 | Celanese Corporation | Continuous fermentation process and bioconversion-product recovery |
EP0129196A2 (en) | 1983-06-15 | 1984-12-27 | BASF Aktiengesellschaft | Process for the continuous production of polyamides |
US4535059A (en) | 1983-01-13 | 1985-08-13 | Celanese Corporation | Muconic acid productivity by a stabilized mutant microorganism population |
US4564594A (en) | 1983-06-30 | 1986-01-14 | E. I. Du Pont De Nemours And Company | Fermentation process for production of carboxylic acids |
US5109104A (en) | 1990-10-04 | 1992-04-28 | E. I. Du Pont De Nemours And Company | Preparation of polyamides from omega-aminonitriles |
US5151543A (en) | 1991-05-31 | 1992-09-29 | E. I. Du Pont De Nemours And Company | Selective low pressure hydrogenation of a dinitrile to an aminonitrile |
US5231016A (en) | 1988-05-02 | 1993-07-27 | Rhone-Poulenc Chimie | Microbiological production of itaconic acid |
US5352825A (en) * | 1993-07-06 | 1994-10-04 | Hoarmann & Reimer Corp. | Recovery of organic acid salts from impure process streams by addition of bases |
US5457040A (en) | 1993-03-12 | 1995-10-10 | Rhone-Poulenc Chimie | Production of itaconic acid by fermentation |
US5487987A (en) | 1993-09-16 | 1996-01-30 | Purdue Research Foundation | Synthesis of adipic acid from biomass-derived carbon sources |
US5824820A (en) | 1995-06-21 | 1998-10-20 | Rhone-Poulenc Chimie | Process for the preparation of citraconic anhydride |
WO2000024808A1 (en) | 1998-10-26 | 2000-05-04 | E.I. Du Pont De Nemours And Company | Continuous polymerization process for preparing polyamides from omega-aminonitriles |
US6238896B1 (en) | 1997-02-20 | 2001-05-29 | Mitsubishi Rayon Co., Ltd. | Process for producing malonic acid derivatives |
US6794165B2 (en) | 1999-02-19 | 2004-09-21 | E. I. Du Pont De Nemours And Company | Biological method for the production of adipic acid and intermediates |
US6825379B2 (en) * | 2001-08-14 | 2004-11-30 | Chemaxz International Corporation | Method for recovering and producing C4-C6 dicarboxylate from alkaline waste solution generated in caprolactam preparation process |
US6958381B2 (en) | 2000-11-23 | 2005-10-25 | Basf Aktiengesellschaft | Polyamide |
US7132562B2 (en) | 2003-11-12 | 2006-11-07 | Invista North America S.A R.L. | Use of modifiers in a dinitrile hydrogenation process |
US20080060948A1 (en) | 2004-09-03 | 2008-03-13 | Goetheer Earl L V | Process and Apparatus for the Production and Separation of Fermentation Products |
WO2009113853A2 (en) | 2008-03-11 | 2009-09-17 | Dsm Ip Assets B.V. | Adipate (ester or thioester) synthesis |
US20090305364A1 (en) | 2008-03-27 | 2009-12-10 | Genomatica, Inc. | Microorganisms for the production of adipic acid and other compounds |
WO2010003728A1 (en) | 2008-07-08 | 2010-01-14 | Dsm Ip Assets B.V. | Dicarboxylic acid production by fermentation at low ph |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5365824B2 (en) * | 2006-03-23 | 2013-12-11 | 独立行政法人産業技術総合研究所 | Method for producing dialkyl succinate and method for producing 1,4-butanediol |
-
2011
- 2011-04-14 US US13/086,801 patent/US8895779B2/en not_active Expired - Fee Related
- 2011-04-15 JP JP2013508004A patent/JP2013530935A/en active Pending
- 2011-04-15 WO PCT/US2011/032613 patent/WO2011136941A1/en active Application Filing
- 2011-04-15 CN CN2011800320593A patent/CN103153931A/en active Pending
- 2011-04-15 KR KR1020127030813A patent/KR20130003031A/en not_active Application Discontinuation
- 2011-04-21 CA CA2738166A patent/CA2738166C/en not_active Expired - Fee Related
- 2011-05-02 EP EP11164486A patent/EP2383250A1/en not_active Withdrawn
- 2011-05-02 BR BRPI1102061-0A patent/BRPI1102061A2/en not_active IP Right Cessation
Patent Citations (47)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB532938A (en) | 1939-06-02 | 1941-02-04 | Rhone Poulenc Sa | Process for the manufacture of adipic nitrile |
US2288687A (en) | 1939-06-07 | 1942-07-07 | Celanese Corp | Manufacture of dinitriles |
GB778253A (en) | 1955-02-02 | 1957-07-03 | Inventa Ag | Process for the manufacture of -e-caprolactam |
US2912363A (en) | 1955-11-28 | 1959-11-10 | Nat Distillers Chem Corp | Fumaric acid fermentation process |
US3063910A (en) | 1960-02-03 | 1962-11-13 | Kyowa Hakko Kogyo Kk | Method of producing l-malic acid by fermentation |
GB1050639A (en) | 1963-09-17 | |||
US3433830A (en) | 1964-09-30 | 1969-03-18 | Chevron Res | Aliphatic dicarboxylic acid purification process |
US3661995A (en) | 1968-01-31 | 1972-05-09 | Ici Ltd | Process for the manufacture of alpha,omega-aliphatic diamines |
DE1904613A1 (en) | 1968-01-31 | 1969-09-04 | Ici Ltd | Process for the preparation of an aliphatic diamine |
US4082788A (en) * | 1968-10-10 | 1978-04-04 | El Paso Products Company | Esterification and extraction process |
US3671566A (en) | 1969-04-01 | 1972-06-20 | Basf Ag | Manufacture of adiponitrile |
DE1916601A1 (en) | 1969-04-01 | 1970-10-29 | Basf Ag | Process for the production of adipic dinitrile |
US4105856A (en) * | 1970-09-29 | 1978-08-08 | El Paso Products Company | Recovery process for aqueous waste streams in adipic acid systems |
CA999013A (en) | 1971-06-25 | 1976-10-26 | Du Pont Of Canada Limited | Preparation of hexamethylene diamine |
DE2639002A1 (en) | 1971-06-25 | 1978-03-09 | Du Pont Canada | Hexa:methylene-di:amine prepn. from 2-cyano-cyclopentanone - by catalytic reaction with ammonia and hydrogen |
US3873425A (en) | 1971-11-19 | 1975-03-25 | Tatsuyoshi Kobayashi | Process for producing itaconic acid |
US4052441A (en) * | 1974-10-10 | 1977-10-04 | Josef Klemens Brunner | Separation of acids and esters in the processing of waste salt solution of cyclohexanone manufacture |
DE2718363A1 (en) | 1977-04-25 | 1978-10-26 | Roehm Gmbh | Carboxylic acid prepn. from their ammonium salts - by heating in aprotic, dipolar solvent contg. oxygen, to remove ammonia |
US4238603A (en) | 1977-05-19 | 1980-12-09 | Monsanto Company | Polyamides derived from hexamethylene diamine, terephthalic acid, isophthalic acid and a C5 to C10 aliphatic dibasic acid |
DE2729421A1 (en) | 1977-06-29 | 1979-01-11 | Du Pont Deutschland | Polyamide prodn. from adipic acid and hexa:methylene:di:amine - using aq. monomeric nylon salt soln. made using recycle condensate from the autoclave and evapn. stages |
US4254283A (en) | 1979-06-07 | 1981-03-03 | Monsanto Company | Process for preparing adipic acid with recovery of glutaric and succinic acids |
US4339536A (en) | 1979-06-08 | 1982-07-13 | Nippon Mining Co., Ltd. | Process for the preparation of long-chain dicarboxylic acids by fermentation |
US4271315A (en) * | 1979-11-15 | 1981-06-02 | El Paso Products Company | Treatment of waste stream from adipic acid manufacture |
US4400468A (en) | 1981-10-05 | 1983-08-23 | Hydrocarbon Research Inc. | Process for producing adipic acid from biomass |
US4480034A (en) | 1982-06-10 | 1984-10-30 | Celanese Corporation | Continuous fermentation process and bioconversion-product recovery |
US4535059A (en) | 1983-01-13 | 1985-08-13 | Celanese Corporation | Muconic acid productivity by a stabilized mutant microorganism population |
EP0129196A2 (en) | 1983-06-15 | 1984-12-27 | BASF Aktiengesellschaft | Process for the continuous production of polyamides |
US4540772A (en) | 1983-06-15 | 1985-09-10 | Basf Aktiengesellschaft | Continuous preparation of nylon from aqueous salt solution in precondensation zone having baffles |
US4564594A (en) | 1983-06-30 | 1986-01-14 | E. I. Du Pont De Nemours And Company | Fermentation process for production of carboxylic acids |
US5231016A (en) | 1988-05-02 | 1993-07-27 | Rhone-Poulenc Chimie | Microbiological production of itaconic acid |
US5109104A (en) | 1990-10-04 | 1992-04-28 | E. I. Du Pont De Nemours And Company | Preparation of polyamides from omega-aminonitriles |
US5151543A (en) | 1991-05-31 | 1992-09-29 | E. I. Du Pont De Nemours And Company | Selective low pressure hydrogenation of a dinitrile to an aminonitrile |
US5457040A (en) | 1993-03-12 | 1995-10-10 | Rhone-Poulenc Chimie | Production of itaconic acid by fermentation |
US5352825A (en) * | 1993-07-06 | 1994-10-04 | Hoarmann & Reimer Corp. | Recovery of organic acid salts from impure process streams by addition of bases |
US5487987A (en) | 1993-09-16 | 1996-01-30 | Purdue Research Foundation | Synthesis of adipic acid from biomass-derived carbon sources |
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US6238896B1 (en) | 1997-02-20 | 2001-05-29 | Mitsubishi Rayon Co., Ltd. | Process for producing malonic acid derivatives |
WO2000024808A1 (en) | 1998-10-26 | 2000-05-04 | E.I. Du Pont De Nemours And Company | Continuous polymerization process for preparing polyamides from omega-aminonitriles |
US6794165B2 (en) | 1999-02-19 | 2004-09-21 | E. I. Du Pont De Nemours And Company | Biological method for the production of adipic acid and intermediates |
US6958381B2 (en) | 2000-11-23 | 2005-10-25 | Basf Aktiengesellschaft | Polyamide |
US6825379B2 (en) * | 2001-08-14 | 2004-11-30 | Chemaxz International Corporation | Method for recovering and producing C4-C6 dicarboxylate from alkaline waste solution generated in caprolactam preparation process |
US7132562B2 (en) | 2003-11-12 | 2006-11-07 | Invista North America S.A R.L. | Use of modifiers in a dinitrile hydrogenation process |
US20080060948A1 (en) | 2004-09-03 | 2008-03-13 | Goetheer Earl L V | Process and Apparatus for the Production and Separation of Fermentation Products |
WO2009113853A2 (en) | 2008-03-11 | 2009-09-17 | Dsm Ip Assets B.V. | Adipate (ester or thioester) synthesis |
US20090305364A1 (en) | 2008-03-27 | 2009-12-10 | Genomatica, Inc. | Microorganisms for the production of adipic acid and other compounds |
WO2010003728A1 (en) | 2008-07-08 | 2010-01-14 | Dsm Ip Assets B.V. | Dicarboxylic acid production by fermentation at low ph |
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"ATCC® Number: 24887(TM)," ATCC-The Global Bioresouce Center-Search Catalog, website printout http://www.atcc.org/ATCCAdvancedCatalogSearch/ProductDetails/tabid/452/Default.aspx?ATCCNum=. . . dated Mar. 30, 2010, 2 pages. |
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Magnuson, J.K. et al., "Organic Acid Production by Filamentous Fungi," Advances in Fungal Biotechnology for Industry, Agriculture, and Medicine, 2004, pp. 307-340. |
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US20130150551A1 (en) * | 2010-06-16 | 2013-06-13 | Bioamber S.A.S. | Processes for the production of hydrogenated products and derivatives thereof |
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